New Bicyclic Azalide Macrolides Obtained by Tandem Palladium Catalyzed Allylic Alkylation/Conjugated Addition Reaction
Abstract
:1. Introduction
2. Results and Discussion
3. Experimental Section
3.1. General Methods
3.2. Synthetic Procedures
- 9-Deoxo-9a-(3-(3-Quinolyl)-2-propenyl)-9a-aza-9a-homoerythromycin A (3)
- Methyl 3-(2-quinolynyl)-Acrylate (6a)
- Methyl 3-(4-quinolynyl)-acrylate (6b)
- 3-(4-Quinolyl)-2-propene-1-ol (7b) [21]
- 3-(2-Quinolinyl)-2-propene-1-ol (7a) [22].
- 3-(4-Quinolyl)-allyl tert-butyl carbonate (8b).
- 3-(2-Quinolyl)-allyl tert-butyl carbonate (8a).
- Methyl 4-hydroxycrotonate (13a) [26]
- 4-Hydroxycrotononitrile (13b)
- Methyl-4-tert-butyloxycarbonyloxy-crotonate (14a)
- 4-tert-Butyloxycarbonyloxy-crotononitrile (14b)
- (22R)-9-Deoxo-11-deoxy-11-9a-(epoxyethano)-22-(2-quinolyl)methyl-9a-aza-9a-homoerythromycin A (10a)
- (22R)-9-Deoxo-11-deoxy-11-9a-(epoxyethano)-22-(4-quinolyl)methyl-9a-aza-9a-homoerythromycin A (10b)
- (22R)-9-Deoxo-11-deoxy-11-9a-(epoxyethano)-22-(methoxycarbonyl)methyl-9a-aza-9a-homoerythromycin A (15a)
- (22R)-9-Deoxo-11-deoxy-11-9a-(epoxyethano)-22-(cyano)methyl-9a-aza-9a-homoerythromycin A (15a)
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Data Availability Statement
Acknowledgments
Conflicts of Interest
References
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Microorganism | MIC (µg/mL) | ||||||
---|---|---|---|---|---|---|---|
Azithromycin | 3 | 10a | 10b | 15a | 15b | ||
S. pneumoniae SP030 | ery S | ≤0.125 | ≤0.125 | ≤0.125 | ≤0.125 | ≤0.125 | ≤0.125 |
S. pyogenes 3565 | ery S | ≤0.125 | ≤0.125 | ≤0.125 | ≤0.125 | 0.25 | 0.25 |
S. aureus ATCC13709 | ery S | 0.5 | 0.25 | ≤0.125 | 0.25 | 4 | 8 |
S. pneumoniae Ci137 | M | 8 | 8 | 4 | 16 | 32 | 32 |
S. pyogenes Finland 2 | M | 8 | 4 | 2 | 4 | 16 | 8 |
S. aureus PK1 | M | >64 | >64 | >64 | >64 | >64 | >64 |
S. pneumoniae 134 GR-M | iMcLS | >64 | >64 | >64 | >64 | >64 | >64 |
S. pyogenes Finland 11 | iMLS | 16 | 2 | 0.5 | 4 | >64 | >64 |
S. aureus PK2 | iMLS | >64 | >64 | >64 | >64 | >64 | >64 |
M. catarrhalis ATCC 49247 | ≤0.125 | 1 | 4 | 4 | 0.5 | 1.25 | |
H. influenzae ATCC 23246 | 1 | 2 | 4 | 4 | 4 | 4 |
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Alihodžić, S.; Čipčić Paljetak, H.; Čikoš, A.; Elenkov, I.J. New Bicyclic Azalide Macrolides Obtained by Tandem Palladium Catalyzed Allylic Alkylation/Conjugated Addition Reaction. Molecules 2022, 27, 432. https://doi.org/10.3390/molecules27020432
Alihodžić S, Čipčić Paljetak H, Čikoš A, Elenkov IJ. New Bicyclic Azalide Macrolides Obtained by Tandem Palladium Catalyzed Allylic Alkylation/Conjugated Addition Reaction. Molecules. 2022; 27(2):432. https://doi.org/10.3390/molecules27020432
Chicago/Turabian StyleAlihodžić, Sulejman, Hana Čipčić Paljetak, Ana Čikoš, and Ivaylo Jivkov Elenkov. 2022. "New Bicyclic Azalide Macrolides Obtained by Tandem Palladium Catalyzed Allylic Alkylation/Conjugated Addition Reaction" Molecules 27, no. 2: 432. https://doi.org/10.3390/molecules27020432